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Yoichiro Ito - One of the best experts on this subject based on the ideXlab platform.
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Preparative separation of di- and trisulfonated components of Quinoline Yellow using affinity-ligand pH-zone-refining counter-current chromatography
Journal of chromatography. A, 2009Co-Authors: Adrian Weisz, Eugene P Mazzola, Yoichiro ItoAbstract:Four positionally isomeric 2-(2-quinolinyl)-1H-indene-1,3(2H)-dionedisulfonic acids (SA) and one triSA, components of the color additive Quinoline Yellow (QY, Color Index No. 47005), were isolated from the dye mixture by affinity-ligand pH-zone-refining counter-current chromatography (CCC) through complementary use of ion-exchange and ion-pair reagents as the ligand. The added ligands facilitated the partitioning of the very polar polysulfonated components into the organic stationary phase of the two-phase solvent systems that consisted of isoamyl alcohol–methyl tert-butyl ether–acetonitrile–water (3:5:1:7), (3:4:1:7) or (3:1:1:5). Thus, separation of a 5-g portion of QY using sulfuric acid as the retainer and dodecylamine as the ligand (an ion-exchange reagent, 20% in the stationary phase), resulted in 1.21 g of 6′,5-diSA and 1.69 g of 6′,8′,5-triSA, both of over 99% purity. A minor component, 8′,4-diSA, not previously reported was also obtained (4.8 mg of over 94% purity) through a similar separation of a different batch of QY using hydrochloric acid as the retainer and 10% dodecylamine as the ligand in the stationary phase. Two components that co-eluted (0.55 g) in the 5 g separation were separated when trifluoroacetic acid was used as the retainer and tetrabutylammonium hydroxide (an ion-pair reagent) as the ligand. The separation resulted in 20.7 mg of 6′,4-diSA, not previously reported, and 111.8 mg of 8′,5-diSA, both of over 98% purity. The isolated compounds were characterized by high-resolution mass spectrometry and proton nuclear magnetic resonance with correlated spectroscopy assignments.
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Purification of Quinoline Yellow components using high-speed counter-current chromatography by stepwise increasing the flow-rate of the mobile phase.
Journal of chromatography. A, 2003Co-Authors: Hisao Oka, Ken-ichi Harada, Masanao Suzuki, Kiyonaga Fujii, Masato Iwaya, Yuko Ito, Tomomi Goto, Hiroshi Matsumoto, Yoichiro ItoAbstract:Quinoline Yellow (Color Index No. 47005) consists of multiple components that show a large difference in their partition coefficients ( K), ranging from 0.03 to 3.3 in the solvent system tert.-butyl methyl ether (MTBE)-1-butanol-acetonitrile- aqueous 0.1 M trifluoroacetic acid (TFA). Consequently, it requires an excessively long elution time for the simultaneous separation of all components by the standard high-speed counter-current chromatography technique, which uses a constant flow-rate of the mobile phase. In order to overcome this problem, we increased the flow-rate of the mobile phase stepwise from 0.1 to 2.0 mL / min. Using this new procedure, six components (0.2-6.1 mg) were successfully isolated from 25 mg of a commercial Quinoline Yellow preparation in a single run using a two-phase solvent system composed of MTBE-1-butanol- acetonitrile-aqueous 0.1 M TFA (1:3:1:5, v / v). The purified components were analyzed by high-performance liquid chromatography, electrospray ionization mass spectrometry, and nuclear magnetic resonance spectroscopy. 2003 Elsevier Science B.V. All rights reserved.
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Preparative separation of isomeric 2-(2-quinolinyl)-1H-indene-1,3(2H)-dione monosulfonic acids of the color additive D&C Yellow No. 10 (Quinoline Yellow) by pH-zone-refining counter-current chromatography.
Journal of Chromatography A, 2001Co-Authors: Adrian Weisz, Eugene P Mazzola, Jean E Matusik, Yoichiro ItoAbstract:The main components of the color additive D&C Yellow No. 10 (Quinoline Yellow, Color Index No. 47005), 2-(2-quinolinyl)-1H-indene-1,3(2H)-dione-6'-sulfonic acid (6SA) and 2-(2-quinolinyl)-1H-indene-1,3(2H)-dione-8'-sulfonic acid (8SA), were isolated from the dye mixture by pH-zone-refining counter-current chromatography (CCC) in the ion-exchange mode. These positional isomers were separated from a portion of dye using sulfuric acid as the retainer acid and dodecylamine as the ligand (ion exchanger). The added ligand enhanced the partitioning of the hydrophilic components in the organic stationary phase of the two-phase solvent system that consisted of isoamyl alcohol-methyl tert.-butyl ether-acetonitrile-water (3:1:1:5). Thus, separation of 1.8 g of D&C Yellow No. 10 using the above method resulted in 0.6 g of 6SA and 0.18 g of 8SA of over 99% purity. The isolated compounds were characterized by mass spectrometry and proton nuclear magnetic resonance with correlated spectroscopy assignments. The study exemplifies a new field of applications for pH-zone-refining CCC, to the separation of positional isomers of strongly hydrophylic compounds containing sulfonic acid groups.
Adrian Weisz - One of the best experts on this subject based on the ideXlab platform.
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determination of sulphonated quinophthalones in Quinoline Yellow and its lakes using high performance liquid chromatography
Food Additives and Contaminants Part A-chemistry Analysis Control Exposure & Risk Assessment, 2020Co-Authors: Adrian Weisz, India C. James, Marianita PerezgonzalezAbstract:Quinoline Yellow (QY, Colour Index No. 47005) is internationally used as a colour additive in foods, drugs, and cosmetics. The manufacture of QY requires sulphonating quinophthalone, and depending on the degree of sulphonation, various forms of QY result, containing different proportions of quinophthalone mono-, di-, and trisulfonic acid sodium salts (monoSA, diSA, and triSA, respectively). Regulations on the specific composition and uses of QY differ across countries with associated differences in names for QY. The QY form certified for use in the U.S. in drugs and cosmetics is known as DC 0.42 and 1.26%, 6'5diSA; 0.11 and 0.34%, 6'8'diSA; and 0.01 and 0.04%, 6'8'5triSA. The HPLC method was applied successfully to the analysis of 20 Y10 and eight Y10 lake samples. It can be extended to other QY forms such as E104 and Yellow 203 because it enables analysis of 6'8'5triSA. This paper also addresses the implications of the varying structure depictions and CAS numbers of the QY components that are due to the existence of three tautomeric forms of quinophthalone.
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identification of 1 5 naphthyridinophthalone and its quantification in the color additive d c Yellow no 10 Quinoline Yellow using high performance liquid chromatography
Food Additives and Contaminants Part A-chemistry Analysis Control Exposure & Risk Assessment, 2018Co-Authors: Adrian Weisz, India C. James, Eugene P Mazzola, Clark D Ridge, Carl F Ijames, Sanford P MarkeyAbstract:ABSTRACTThe present work reports the identification and characterization of a contaminant, 2-(2ʹ-(1,5-naphthyridinyl))-1,3-indanedione (1ʹ,5ʹ-naphthyridinophthalone, 1,5NP), in the color additive D&C Yellow No. 10 (U.S.-certifiable form of Quinoline Yellow), together with its quantification in batches of the color additive certified by the U.S. Food and Drug Administration (USFDA). The impurity, which is a compound not previously reported in the literature, was synthesised and characterised for use as a reference material. Test portions from 26 certified batches of D&C Yellow No. 10 submitted to USFDA by four domestic and four foreign manufacturers were analyzed for 1,5NP using high-performance liquid chromatography. The results revealed a wide range of 1,5NP levels across batches, with 18 (69.2%) of the test portions containing amounts from 0.32 to 169.94 µg g−1 while the remaining test portions contained no detectable (<0.07 µg g−1) amounts. Samples of the European and Japanese forms of Quinoline Yellow...
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identification of 1 5 naphthyridinophthalone and its quantification in the color additive d c Yellow no 10 Quinoline Yellow using high performance liquid chromatography
Food Additives and Contaminants Part A-chemistry Analysis Control Exposure & Risk Assessment, 2018Co-Authors: Adrian Weisz, India C. James, Eugene P Mazzola, Clark D Ridge, Carl F Ijames, Sanford P MarkeyAbstract:The present work reports the identification and characterization of a contaminant, 2-(2ʹ-(1,5-naphthyridinyl))-1,3-indanedione (1ʹ,5ʹ-naphthyridinophthalone, 1,5NP), in the color additive D&C Yello...
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Preparative separation of di- and trisulfonated components of Quinoline Yellow using affinity-ligand pH-zone-refining counter-current chromatography
Journal of chromatography. A, 2009Co-Authors: Adrian Weisz, Eugene P Mazzola, Yoichiro ItoAbstract:Four positionally isomeric 2-(2-quinolinyl)-1H-indene-1,3(2H)-dionedisulfonic acids (SA) and one triSA, components of the color additive Quinoline Yellow (QY, Color Index No. 47005), were isolated from the dye mixture by affinity-ligand pH-zone-refining counter-current chromatography (CCC) through complementary use of ion-exchange and ion-pair reagents as the ligand. The added ligands facilitated the partitioning of the very polar polysulfonated components into the organic stationary phase of the two-phase solvent systems that consisted of isoamyl alcohol–methyl tert-butyl ether–acetonitrile–water (3:5:1:7), (3:4:1:7) or (3:1:1:5). Thus, separation of a 5-g portion of QY using sulfuric acid as the retainer and dodecylamine as the ligand (an ion-exchange reagent, 20% in the stationary phase), resulted in 1.21 g of 6′,5-diSA and 1.69 g of 6′,8′,5-triSA, both of over 99% purity. A minor component, 8′,4-diSA, not previously reported was also obtained (4.8 mg of over 94% purity) through a similar separation of a different batch of QY using hydrochloric acid as the retainer and 10% dodecylamine as the ligand in the stationary phase. Two components that co-eluted (0.55 g) in the 5 g separation were separated when trifluoroacetic acid was used as the retainer and tetrabutylammonium hydroxide (an ion-pair reagent) as the ligand. The separation resulted in 20.7 mg of 6′,4-diSA, not previously reported, and 111.8 mg of 8′,5-diSA, both of over 98% purity. The isolated compounds were characterized by high-resolution mass spectrometry and proton nuclear magnetic resonance with correlated spectroscopy assignments.
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Preparative separation of isomeric 2-(2-quinolinyl)-1H-indene-1,3(2H)-dione monosulfonic acids of the color additive D&C Yellow No. 10 (Quinoline Yellow) by pH-zone-refining counter-current chromatography.
Journal of Chromatography A, 2001Co-Authors: Adrian Weisz, Eugene P Mazzola, Jean E Matusik, Yoichiro ItoAbstract:The main components of the color additive D&C Yellow No. 10 (Quinoline Yellow, Color Index No. 47005), 2-(2-quinolinyl)-1H-indene-1,3(2H)-dione-6'-sulfonic acid (6SA) and 2-(2-quinolinyl)-1H-indene-1,3(2H)-dione-8'-sulfonic acid (8SA), were isolated from the dye mixture by pH-zone-refining counter-current chromatography (CCC) in the ion-exchange mode. These positional isomers were separated from a portion of dye using sulfuric acid as the retainer acid and dodecylamine as the ligand (ion exchanger). The added ligand enhanced the partitioning of the hydrophilic components in the organic stationary phase of the two-phase solvent system that consisted of isoamyl alcohol-methyl tert.-butyl ether-acetonitrile-water (3:1:1:5). Thus, separation of 1.8 g of D&C Yellow No. 10 using the above method resulted in 0.6 g of 6SA and 0.18 g of 8SA of over 99% purity. The isolated compounds were characterized by mass spectrometry and proton nuclear magnetic resonance with correlated spectroscopy assignments. The study exemplifies a new field of applications for pH-zone-refining CCC, to the separation of positional isomers of strongly hydrophylic compounds containing sulfonic acid groups.
K Ichihashi - One of the best experts on this subject based on the ideXlab platform.
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determination of 40 synthetic food colors in drinks and candies by high performance liquid chromatography using a short column with photodiode array detection
Talanta, 2008Co-Authors: N Yoshioka, K IchihashiAbstract:Abstract Forty synthetic food colors were determined in drinks and candies by reversed-phase high-performance liquid chromatography with photodiode array detection. The following food colors were analyzed within 19 min using a short analytical column (50 mm × 4.6 mm i.d., 1.8 μm) at 50 °C with gradient elution: Ponceau 6R, Tartrazine, Fast Yellow AB, Amaranth, Indigotine, Naphthol Yellow S, Chrysoine, Ponceau 4R, Sunset Yellow FCF, Red 10B, Orange G, Acid violet 7, Brilliant black PN, Allura red AC, Yellow 2G, Red 2G, Uranine, Fast red E, Green S, Ponceau 2R, Azorubine, Orange I, Quinoline Yellow, Martius Yellow, Ponceau SX, Ponceau 3R, Fast green FCF, Eosine, Brilliant blue FCF, Orange II, Orange RN, Acid blue 1, Erythrosine, Amido black 10B, Acid red 52, Patent blue V, Acid green 9, Phloxine B, Benzyl violet 4B, and Rose bengal. The recoveries of these compounds added to soft drinks and candies at 5 μg/g ranged from 76.6 to 115.0%, and relative standard deviations (R.S.D.s) were within 6.0%. The limits of detection and the limits of quantitation were 0.03 and 0.1 μg/g, respectively.
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determination of 40 synthetic food colors in drinks and candies by high performance liquid chromatography using a short column with photodiode array detection
Talanta, 2008Co-Authors: N Yoshioka, K IchihashiAbstract:Forty synthetic food colors were determined in drinks and candies by reversed-phase high-performance liquid chromatography with photodiode array detection. The following food colors were analyzed within 19 min using a short analytical column (50 mm x 4.6 mm i.d., 1.8 microm) at 50 degrees C with gradient elution: Ponceau 6R, Tartrazine, Fast Yellow AB, Amaranth, Indigotine, Naphthol Yellow S, Chrysoine, Ponceau 4R, Sunset Yellow FCF, Red 10B, Orange G, Acid violet 7, Brilliant black PN, Allura red AC, Yellow 2G, Red 2G, Uranine, Fast red E, Green S, Ponceau 2R, Azorubine, Orange I, Quinoline Yellow, Martius Yellow, Ponceau SX, Ponceau 3R, Fast green FCF, Eosine, Brilliant blue FCF, Orange II, Orange RN, Acid blue 1, Erythrosine, Amido black 10B, Acid red 52, Patent blue V, Acid green 9, Phloxine B, Benzyl violet 4B, and Rose bengal. The recoveries of these compounds added to soft drinks and candies at 5 microg/g ranged from 76.6 to 115.0%, and relative standard deviations (R.S.D.s) were within 6.0%. The limits of detection and the limits of quantitation were 0.03 and 0.1 microg/g, respectively.
Eugene P Mazzola - One of the best experts on this subject based on the ideXlab platform.
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identification of 1 5 naphthyridinophthalone and its quantification in the color additive d c Yellow no 10 Quinoline Yellow using high performance liquid chromatography
Food Additives and Contaminants Part A-chemistry Analysis Control Exposure & Risk Assessment, 2018Co-Authors: Adrian Weisz, India C. James, Eugene P Mazzola, Clark D Ridge, Carl F Ijames, Sanford P MarkeyAbstract:ABSTRACTThe present work reports the identification and characterization of a contaminant, 2-(2ʹ-(1,5-naphthyridinyl))-1,3-indanedione (1ʹ,5ʹ-naphthyridinophthalone, 1,5NP), in the color additive D&C Yellow No. 10 (U.S.-certifiable form of Quinoline Yellow), together with its quantification in batches of the color additive certified by the U.S. Food and Drug Administration (USFDA). The impurity, which is a compound not previously reported in the literature, was synthesised and characterised for use as a reference material. Test portions from 26 certified batches of D&C Yellow No. 10 submitted to USFDA by four domestic and four foreign manufacturers were analyzed for 1,5NP using high-performance liquid chromatography. The results revealed a wide range of 1,5NP levels across batches, with 18 (69.2%) of the test portions containing amounts from 0.32 to 169.94 µg g−1 while the remaining test portions contained no detectable (<0.07 µg g−1) amounts. Samples of the European and Japanese forms of Quinoline Yellow...
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identification of 1 5 naphthyridinophthalone and its quantification in the color additive d c Yellow no 10 Quinoline Yellow using high performance liquid chromatography
Food Additives and Contaminants Part A-chemistry Analysis Control Exposure & Risk Assessment, 2018Co-Authors: Adrian Weisz, India C. James, Eugene P Mazzola, Clark D Ridge, Carl F Ijames, Sanford P MarkeyAbstract:The present work reports the identification and characterization of a contaminant, 2-(2ʹ-(1,5-naphthyridinyl))-1,3-indanedione (1ʹ,5ʹ-naphthyridinophthalone, 1,5NP), in the color additive D&C Yello...
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Preparative separation of di- and trisulfonated components of Quinoline Yellow using affinity-ligand pH-zone-refining counter-current chromatography
Journal of chromatography. A, 2009Co-Authors: Adrian Weisz, Eugene P Mazzola, Yoichiro ItoAbstract:Four positionally isomeric 2-(2-quinolinyl)-1H-indene-1,3(2H)-dionedisulfonic acids (SA) and one triSA, components of the color additive Quinoline Yellow (QY, Color Index No. 47005), were isolated from the dye mixture by affinity-ligand pH-zone-refining counter-current chromatography (CCC) through complementary use of ion-exchange and ion-pair reagents as the ligand. The added ligands facilitated the partitioning of the very polar polysulfonated components into the organic stationary phase of the two-phase solvent systems that consisted of isoamyl alcohol–methyl tert-butyl ether–acetonitrile–water (3:5:1:7), (3:4:1:7) or (3:1:1:5). Thus, separation of a 5-g portion of QY using sulfuric acid as the retainer and dodecylamine as the ligand (an ion-exchange reagent, 20% in the stationary phase), resulted in 1.21 g of 6′,5-diSA and 1.69 g of 6′,8′,5-triSA, both of over 99% purity. A minor component, 8′,4-diSA, not previously reported was also obtained (4.8 mg of over 94% purity) through a similar separation of a different batch of QY using hydrochloric acid as the retainer and 10% dodecylamine as the ligand in the stationary phase. Two components that co-eluted (0.55 g) in the 5 g separation were separated when trifluoroacetic acid was used as the retainer and tetrabutylammonium hydroxide (an ion-pair reagent) as the ligand. The separation resulted in 20.7 mg of 6′,4-diSA, not previously reported, and 111.8 mg of 8′,5-diSA, both of over 98% purity. The isolated compounds were characterized by high-resolution mass spectrometry and proton nuclear magnetic resonance with correlated spectroscopy assignments.
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Preparative separation of isomeric 2-(2-quinolinyl)-1H-indene-1,3(2H)-dione monosulfonic acids of the color additive D&C Yellow No. 10 (Quinoline Yellow) by pH-zone-refining counter-current chromatography.
Journal of Chromatography A, 2001Co-Authors: Adrian Weisz, Eugene P Mazzola, Jean E Matusik, Yoichiro ItoAbstract:The main components of the color additive D&C Yellow No. 10 (Quinoline Yellow, Color Index No. 47005), 2-(2-quinolinyl)-1H-indene-1,3(2H)-dione-6'-sulfonic acid (6SA) and 2-(2-quinolinyl)-1H-indene-1,3(2H)-dione-8'-sulfonic acid (8SA), were isolated from the dye mixture by pH-zone-refining counter-current chromatography (CCC) in the ion-exchange mode. These positional isomers were separated from a portion of dye using sulfuric acid as the retainer acid and dodecylamine as the ligand (ion exchanger). The added ligand enhanced the partitioning of the hydrophilic components in the organic stationary phase of the two-phase solvent system that consisted of isoamyl alcohol-methyl tert.-butyl ether-acetonitrile-water (3:1:1:5). Thus, separation of 1.8 g of D&C Yellow No. 10 using the above method resulted in 0.6 g of 6SA and 0.18 g of 8SA of over 99% purity. The isolated compounds were characterized by mass spectrometry and proton nuclear magnetic resonance with correlated spectroscopy assignments. The study exemplifies a new field of applications for pH-zone-refining CCC, to the separation of positional isomers of strongly hydrophylic compounds containing sulfonic acid groups.
Ghazaleh Mogaddam - One of the best experts on this subject based on the ideXlab platform.
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development of a green chromatographic method for simultaneous determination of food colorants
Food Analytical Methods, 2012Co-Authors: Mahnaz Khanavi, Mohammad Reza Oveisi, Mohammad Reza Shams Ardekani, Ali Mohammad Ranjbar, Mannan Hajimahmoodi, Ghazaleh MogaddamAbstract:A green chromatographic method for the successful separation and determination of eight synthetic food colorants (Tartrazine E 102, Quinoline Yellow E 104, Sunset Yellow E 110, Carmoisine E 122, Ponceau 4R E 124, Allura Red E 129, Indigo Carmine E 132 and Brilliant Blue E 133) was developed. A C8 stationary phase was used and the mobile phase was a mixture of 50 mM phosphate buffer at pH 7 containing triton X-100 (0.25% v/v). The method was validated as regards its selectivity, linearity, precision, accuracy, limit of detection (LOD) and quantification (LOQ). LOD of colorants varied between 0.17 μg mL−1 in Allura Red and 1.91 μg mL−1 in Quinoline Yellow. In the case of LOQ, it was ranged from 0.52 in the Allura Red to 5.79 in the Quinoline Yellow. The method applicability was verified by the determination of colorants present in 22 samples. The 15 samples were only unicolor and the color concentration in these samples varied from 18.426 ± 0.100 to 610.390 ± 4.711 ppm. The method can be used successfully to the determination of binary and ternary color food and drug samples too. This method provides substantial green benefits without using organic solvents in extraction procedure and in both liquid and paper chromatographic methods.
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development of a green chromatographic method for simultaneous determination of food colorants
Food Analytical Methods, 2012Co-Authors: Mahnaz Khanavi, Mohammad Reza Oveisi, Mohammad Reza Shams Ardekani, Ali Mohammad Ranjbar, Mannan Hajimahmoodi, Ghazaleh MogaddamAbstract:A green chromatographic method for the successful separation and determination of eight synthetic food colorants (Tartrazine E 102, Quinoline Yellow E 104, Sunset Yellow E 110, Carmoisine E 122, Ponceau 4R E 124, Allura Red E 129, Indigo Carmine E 132 and Brilliant Blue E 133) was developed. A C8 stationary phase was used and the mobile phase was a mixture of 50 mM phosphate buffer at pH 7 containing triton X-100 (0.25% v/v). The method was validated as regards its selectivity, linearity, precision, accuracy, limit of detection (LOD) and quantification (LOQ). LOD of colorants varied between 0.17 μg mL−1 in Allura Red and 1.91 μg mL−1 in Quinoline Yellow. In the case of LOQ, it was ranged from 0.52 in the Allura Red to 5.79 in the Quinoline Yellow. The method applicability was verified by the determination of colorants present in 22 samples. The 15 samples were only unicolor and the color concentration in these samples varied from 18.426 ± 0.100 to 610.390 ± 4.711 ppm. The method can be used successfully to the determination of binary and ternary color food and drug samples too. This method provides substantial green benefits without using organic solvents in extraction procedure and in both liquid and paper chromatographic methods.
